Ask anyone what the best things to do in Chicago are, and you’ll get a different answer every time, and they’re probably all right. The Ledge at Skydeck isn’t the only thing that brings people from around the world to the Windy City. Chicago offers an impressive mix of iconic landmarks, cultural institutions, outdoor spaces, Chicago activities, and neighborhood experiences. Whether you want to admire Lake Michigan, visit Millennium Park’s Cloud Gate, explore the Chicago Riverwalk, shop along Michigan Avenue’s Magnificent Mile, or spend a day at one of the city’s renowned museum campuses, there is no shortage of fun things to do in Chicago. Use the sections below to explore top Chicago attractions, plan your visit, and discover experiences for every season.
Quick Summary: The best things to do in Chicago span iconic sights and attractions like Willis Tower’s Skydeck, Millennium Park, and the Chicago Riverwalk, distinct neighborhoods like the Loop, River North, and Wrigleyville, and a full calendar of seasonal events from the Chicago Auto Show to Lincoln Park Zoolights. Add in the city’s famous food scene, romantic date-night spots, and practical planning tips, and there’s enough here to fill a single day downtown or a multi-day visit.
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Skydeck Chicago Attractions
Skydeck Chicago is one of the city’s most iconic attractions, offering unmatched views from the top of Willis Tower. From stepping onto The Ledge’s glass floor balconies to exploring the Chicago Museum’s immersive exhibits on the city’s history and architecture, Skydeck delivers one of the best things to do in Chicago for first-time and returning visitors alike. Want to make it a meal with a view? Pie in the Sky adds a food and drink experience right alongside the skyline. Looking for things to do near Skydeck itself? Pair your visit with a walk through the Loop, just steps from Willis Tower’s front doors.
Plan Your Day
Not sure where to start? These guides help you map out an itinerary, whether you’ve got a full weekend or just one day downtown.
- Chicago Itinerary: What to Do If You Have One Day Downtown: A step-by-step plan for making the most of a single day.
- A Perfect Chicago Day: Wrigley Field & Skydeck Chicago: Pair a Cubs game with a trip up Willis Tower.
The Sights
Chicago is home to some of the most recognizable Chicago attractions in the country, from iconic architecture and landmark venues to scenic waterfront views. This section highlights the must-see sights and top attractions that belong on every first-time and repeat visitor’s itinerary.
- Must-See Tourist Attractions: The landmarks that belong on every Chicago itinerary.
- The Most Famous Chicago Skyscrapers: Meet the buildings that define the city’s skyline.
- Famous Places in Chicago: The spots visitors recognize before they even arrive.
- What is the Magnificent Mile?: Chicago’s premier shopping and dining stretch on Michigan Avenue.
- What is the Bean?: The story behind Millennium Park’s famous mirrored sculpture.
- What is Buckingham Fountain?: Grant Park’s iconic centerpiece, best seen during its evening light shows.
- What is the Chicago Riverwalk?: Dining, boating, and skyline views along the water.
- Millennium Park: Home of the Bean, Crown Fountain, and the Pritzker Pavilion.
- Navy Pier: Rides, dining, and skyline views out on the lakefront.
- Best Museums in Chicago: Where to go for art, science, and history in one trip.
- Chicago Architecture and Tours: How to see the skyline and riverfront through a local’s eyes.
- Chicago Theaters: Touring Broadway shows and long-running Chicago originals.
- Guaranteed Rate Field: Home of the Chicago White Sox on the city’s south side.
- Soldier Field: Home of the Chicago Bears, right along the lakefront.
- Chicago Live Cams: Watch the city skyline in real time before you visit.
- Best Parks in Chicago: Green space picks from downtown to the neighborhoods.
- Beaches: Where to catch some sun and swim along Lake Michigan.
Chicago Neighborhoods
Every Chicago neighborhood has its own personality, from historic architecture to nightlife and local dining. Explore some of the city’s most visited areas.
- Chicago Neighborhood Guide: An overview of the city’s most notable neighborhoods.
- The Loop: Downtown Chicago’s business, financial, and cultural core.
- River North: Art galleries, nightlife, and dining just north of the river.
- Wrigleyville: The lively neighborhood surrounding Wrigley Field.
- Lincoln Park: A lakefront neighborhood known for its park, zoo, and nightlife.
- West Loop: A dining destination packed with some of the city’s top restaurants.
- Bucktown: A trendy North Side neighborhood known for boutiques and nightlife.
- Logan Square: A leafy, artsy neighborhood with some of the city’s best food.
- Wicker Park: Vintage shops, live music, and a strong indie streak.
- Ukrainian Village: A historic, close-knit neighborhood with standout local dining.
Tips
Planning ahead can make a big difference when exploring the best things to do in Chicago. Use these practical travel tips to navigate the city, manage your time efficiently, and maximize your overall experience.
- Is Chicago Safe to Visit?: What visitors should know before their trip.
- Can You Visit Skydeck Chicago at Night?: What the view looks like after dark, and when to go.
- Chicago Airports: O’Hare vs. Midway Guide: Which airport to fly into for your trip downtown.
Chicago Trivia & History
Curious about the stories behind the city? These guides dig into where Chicago’s name and nicknames came from, and what makes the city tick.
- What Does “Chicago” Mean?: The origin story behind the city’s name.
- Why is Chicago Called “The Windy City”?: The real story behind the nickname, and it’s not the weather.
- Why is Chicago Called “The Second City”?: The story behind one of Chicago’s most enduring nicknames.
- What is Chicago Known For?: The food, landmarks, sports, and culture that define the city.
Want more? Browse even more Chicago fun facts, from the city’s population growth to why the river turns green every March.
Seasonal Activities
Chicago has something to offer no matter when you visit. Browse these seasonal activity ideas to build an itinerary based on the time of year, your interests, and your pace.
- Winter Activities Winter: Cold-weather things to do, from ice skating to indoor attractions.
- Sledding Hills Winter: The best spots around the city for a snow day.
- Chicago in December Winter: Weather, holiday events, and things to do, including Holidays at Skydeck.
- Summer Activities Summer: Outdoor picks for Chicago’s warmest months.
- Chicago Summer Bucket List Summer: Everything to check off before summer ends.
- Chicago Summer Staycation Guide Summer: A local’s guide to making the most of summer in the city.
- Spooky Things to Do in Chicago for Halloween Fall: Haunted houses, ghost tours, and seasonal events around the city.
Date & Proposal Ideas
Planning something romantic? These guides cover date ideas, proposal spots, and seasonal picks for couples exploring Chicago together.
- Romantic Things to Do: Chicago’s best spots for a memorable date.
- Proposal Ideas: Scenic, unforgettable spots to pop the question.
- Best Places to Celebrate an Anniversary in Chicago: Memorable spots for marking the occasion.
- Best Places to See the Sunset in Chicago: The city’s best golden-hour views.
- Winter Date Ideas Winter: Cozy, cold-weather date ideas around the city.
- Spring Date Ideas Spring: Fresh-air date ideas as the city thaws out.
- Summer Date Ideas Summer: Warm-weather outings for couples.
Food
Chicago’s food scene is a destination in itself, known for iconic dishes and diverse dining neighborhoods. Explore where to eat, what to try, and how to experience the city’s most famous flavors.
- Famous Chicago Foods: The dishes every visitor should try at least once.
- Where to Eat Near Willis Tower: Dining picks within walking distance of Skydeck.
- What is Chicago-Style Pizza?: A guide to the city’s iconic deep dish.
- How to Make a Chicago-Style Hot Dog: The toppings that make a Chicago dog a Chicago dog.
- Best Happy Hours in Chicago: Top deals, rooftops, and unique happy hour spots.
Yearly and Seasonal Events
Chicago hosts a full calendar of annual festivals, holiday celebrations, and seasonal events that showcase the city at its best. From summer street festivals to winter traditions and limited-time experiences, these events add even more variety to the best things to do in Chicago throughout the year.
- Chicago Auto Show Feb: One of the largest auto shows in the country, held every February.
- Chicago Summer Street Festivals Guide Summer: A month-by-month roundup of the city’s best neighborhood festivals, from Do Division to Wicker Park Fest.
- Taste of Chicago Summer: The city’s signature food festival in Grant Park.
- Lollapalooza Summer: Four days of major headliners across eight stages in Grant Park in late July / early August.
- Chicago Air and Water Show Summer: Free military and civilian aerial performances along the Lake Michigan lakefront in August.
- Where to See Fall Foliage Fall: The best spots around Chicago for autumn color.
- Riot Fest Fall: Three days of punk, rock, and alternative music at Douglass Park in September.
- Chicago Thanksgiving Parade Nov: A downtown holiday tradition each Thanksgiving morning.
- Lincoln Park Zoolights Winter: A holiday lights display at Lincoln Park Zoo.
Make Your Time in Chicago Special with Skydeck
One of the best ways to elevate your visit is by seeing the city from 1,353 feet above street level at Skydeck Chicago. Located atop Willis Tower, Skydeck offers breathtaking views across the city and up to four states on a clear day. While Chicago is filled with unforgettable experiences, Skydeck provides a one-of-a-kind perspective that enhances any itinerary. Contact us with questions or purchase tickets online to add one of the best things to do in Chicago to your trip.
Things to Do in Chicago FAQs
What Are the Best Things to Do in Chicago for First-Time Visitors?
Start with top Chicago attractions like Skydeck Chicago at Willis Tower, Millennium Park, the Chicago Riverwalk, and the Magnificent Mile. From there, add a museum stop, a neighborhood meal, and one seasonal event to round out your itinerary.
What Are the Most Popular Chicago Attractions?
Popular Chicago attractions include Skydeck Chicago and The Ledge, Millennium Park, Navy Pier, the Art Institute of Chicago, and the Museum Campus. Many visitors also prioritize river architecture tours and lakefront parks for classic city views.
What Are Fun Activities to Do in Chicago?
Fun Chicago activities span sightseeing, food, and entertainment: ride the L through the Loop, walk the Riverwalk, catch a game at Wrigley Field or Guaranteed Rate Field, or spend an afternoon at Skydeck. Add a seasonal event or a neighborhood food crawl to round out the day.
What Are Fun Things to Do in Chicago With Kids?
Families often enjoy interactive museums, lakefront attractions, parks, and sightseeing experiences like Skydeck. Many seasonal events and festivals also offer kid-friendly activities throughout the year. Check out our activities for kids, including coloring pages, quizzes, and a Skydeck scavenger hunt.
What Are Fun Things to Do in Chicago on a Rainy Day?
Consider indoor Chicago attractions like museums, aquariums, immersive exhibits, shopping destinations, and indoor observation experiences. Building a flexible itinerary makes it easy to swap outdoor activities for indoor options when the weather changes.
How Many Days Do You Need to Explore the Best Things to Do in Chicago?
A weekend is enough to cover several highlights, but 3-4 days gives you more time for neighborhoods, museums, and seasonal events. Many visitors plan one major attraction per day and build around it with food, shopping, and sightseeing.
Is Skydeck Chicago Worth It?
Skydeck is a top-rated Chicago attraction and a standout experience for visitors who want panoramic views of the skyline and Lake Michigan. The Ledge, a series of glass floor balconies extending from Willis Tower, is a must-do for many first-time visitors.